US4908399A - Encapsulating compositions - Google Patents

Encapsulating compositions Download PDF

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Publication number
US4908399A
US4908399A US07/270,136 US27013688A US4908399A US 4908399 A US4908399 A US 4908399A US 27013688 A US27013688 A US 27013688A US 4908399 A US4908399 A US 4908399A
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hydrocarbyl
formula
derivative
metal ion
substituted derivative
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Stephen J. Harris
Maureen G. MacManus
John Guthrie
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Henkel Loctite Ireland Ltd
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Henkel Loctite Ireland Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/40—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/549—Silicon-containing compounds containing silicon in a ring

Definitions

  • This invention relates to encapsulating compositions for electronic devices such as semiconductor devices, integrated circuits and microelectronic components.
  • Resin compositions are well known for encapsulating electronic devices. It is also well known that such compositions are often contaminated by trace amounts of metal ions, particularly alkali metal ions. If such metal ions are permitted to migrate in the composition, they can adversely affect the performance of the electronic device and may ultimately lead to device failure. Chloride ions can also give rise to a corrosion problem.
  • crown ether or cryptate ether in such compositions as metal ion scavengers (U.S. Pat. Nos. 4271425 and 4278784 of Ching-Ping Wong, referring to Japanese Patent No. 76-11377 of Kaneda et. al.).
  • crown ethers and cryptate ethers are unsuitable for commercial use because of their high toxicity.
  • the present invention provides an encapsulating composition for electronic devices which comprises a polymeric material and a metal ion scavenger selected from
  • n 0-8;
  • R 3 is H, halogen, or hydrocarbyl, or a substituted derivative thereof, and R 3 may be the same or different on each aryl group;
  • R 4 is hydrocarbyl, hydrocarbyloxy or a substituted derivative thereof
  • R 4 is ##STR4## wherein R 5 and R 6 which may be the same or different are H, or hydrocarbyl or a substituted derivative thereof;
  • R 15 is H or hydrocarbyl or a substituted derivative thereof
  • the calixarene or oxacalixarene derivative being present as a compound per se or being bound into the polymer network of the polymeric material;
  • q is an integer of from 2 to 3000;
  • R 10 is a substituted or unsubstituted alkyl residue having 2 to 6 carbon atoms; the (R 10 --O) groups containing the same alkyl residue or containing 2 or more different alkyl residues which may be distributed on the chain in a random or block manner;
  • R 11 is hydrogen, or hydrocarbyl or a substituted derivative thereof
  • R 9 is hydroxy, or hydrocarbyloxy or a substituted derivative thereof; ##STR6## wherein R 12 is --(R 10 --O) q --R 11 in which R 10 , R 11 and q are as defined above; ##STR7## wherein R 12 is as defined above;
  • R 13 is hydrogen, halogen, or hydrocarbyl or a substituted derivative thereof.
  • x is an integer from 4 to 8;
  • R 10 , R 11 and q are as defined above.
  • hydrocarbyl groups there may be given alkyl, alkenyl, aryl and moieties having both non-aryl hydrocarbyl and aryl hydrocarbyl portions.
  • hydrocarbyloxy groups there may be given non-aryl containing hydrocarbyloxy, aryloxy and oxy moieties having both non-aryl hydrocarbyl and aryl hydrocarbyl portions.
  • the metal ion scavenger is added in an effective amount which may suitably be from 0.5 to 10% by weight, based on the polymeric material.
  • a polymeric material having a calixarene derivative of formula II above incorporated into the polymer network is preferably of the kind described in European patent application No. 0196895A2 which describes, inter alia, polyorganosiloxanes having at least one calixarene group bound thereto.
  • a trialkoxysilyl calixarene derivative of the formula: ##STR9## may be used to crosslink polydimethylsiloxanediol in the presence of a tin salt so that it is incorporated into the cured RTV silicone network.
  • a calixarene derivative bound into a polymer network has the advantage that it cannot leach out during the working life of the encapsulating composition.
  • the non-aryl hydrocarbyl or hydrocarbyloxy groups shall preferably contain from 1 to 10 carbon atoms, more preferably from 1 to 5 carbon atoms and the aromatic hydrocarbyl and aromatic hydrocarbyloxy groups shall preferably have from 6 to 20 carbon atoms, more preferably from 6 to 10 carbon atoms.
  • Non-aryl hydrocarbyl groups are preferred, especially alkyl or alkenyl groups.
  • a substituted derivative of the foregoing may suitably be substituted with one or more halo groups or substituted or interrupted by one or more oxo groups.
  • Halogen may be chlorine, bromine, fluorine or iodine.
  • calixarene derivatives The preparation of calixarene derivatives is known and is described, for example, in C. Gutsche et. al. Acc. Chem. Res., 16, 161-170 (1983); in U.S. Pat. No. 4556700 Harris et al., and in J. Inclusion Phenomena 2 199-206 (1984) D. Reidel Publishing Company.
  • the methyl and ether bridges may or may not alternate within the oxacalixarene molecule.
  • Preferred etherified oxacalixarenes of formula II are
  • Oxacalixarene compounds may be readily synthesised by methods described in C. Gutsche et. al., J. AM. Chem. Soc. 103, 3782 (1981); B. Dhawan et al., J. Org. Chem., 48, 1536 (1983) and U.S. Pat. No. 4 098 717 Buriks et al.
  • Etherified oxacalixarenes of formula II may be produced by reacting a phenolic oxacalixarene with a halomethyl acetone or a haloalkyl acetate. Potassium iodide may be added to accelerate etherification. This method of production and the etherified oxacalixarenes of formula II are the subject of Irish patent application No. 153/87 filed 21 Jan. 1987.
  • Amide-functional calixarenes and oxacalixarenes of formula II may be prepared by methods described in G. Calestani et al., J. Chem. Soc., Chem. Commun., 1987, 344.
  • the amide-functional oxacalixarene derivatives are novel compounds and are covered in an Irish patent application No. 2574/87 entitled "Nitrogen-containing Oxacalixarenes and Calixarene Derivatives and use of such Compounds" filed 24 Sept. 1987.
  • Silacrowns of formula III are commercially available, e.g. from Petrarch Systems, Bristol, Pa., U.S.A. Suitable silacrowns and the preparation thereof are described in B. Arkles et al., "Silacrowns, a New Class of Immobilizable Phase Transfer Catalysts", American Chemical Society Symposium Series No. 192 - Chemically Modified Surfaces in Catalysis and Electrocatalysis, (Joel S. Miller, editor) 1982; and in Organometallics, Vol. 2, No. 3, 1983, 454. Suitable silacrowns include 1,1-dimethylsila-11-crown-4, 1,1-dimethylsila-14-crown-5, and 1,1-dimethylsila-17-crown-6.
  • Polyalkylene ether glycols and ether derivatives thereof are commercially available or can be prepared by well known procedures.
  • the value of q is preferably in the range 2-25, more especially 3-6.
  • Compounds of formula V and VI are covered in our Irish patent application No. 204/87 filed 27 Jan. 1987.
  • Calixarene derivatives of formula VI may be prepared by the processes described in the literature already mentioned above.
  • Cyclotriveratrylene compounds of formula V may be synthesised as described in J. A. Hyatt, J. Org. Chem. 43 1808-1811 (1978), the contents of which are incorporated herein by reference.
  • the polymeric material may be any of the resins known for encapsulating compositions, particularly silicone resins such as RTV silicone resins, and epoxy resins, see for example U.S. Pat. Nos. 4 271 425 and 4 278 784 and Japanese Pat. No. 76-11377.
  • the metal ion scavengers in the compositions of the present invention have a substantial advantage over crown ethers in commercial use because they are of low toxicity.
  • ERL 4221 Electronic Grade (E.G.) which is commercially available from Union Carbide Corporation, Danbury, Conn., U.S.A. and which is believed to be 3,4-epoxycyclohexyl methyl cyclohexanecarboxylate, was added 1 g of the calixarene derivative of Example 1.
  • the composition was stirred well in a polyethylene beaker with PTFE-coated stirrer for 17 hours to effect complete dissolution.
  • Example 2 A formulation of 100 g of epoxy resin Quatrex 1010 which is commercially available from The Dow Chemical Company, Midland, Mich., U.S.A. and which is believed to be diglycidyl ether of Bisphenol A (low hydrolysable chloride level), and 1 g of the calixarene derivative of Example 1 was prepared as above in Example 2.
  • a formulation consisting of 100 g epoxy Quatrex 1010 and 1 g of 18-crown-6 was prepared as in Example 3.
  • Example 2 To 10 g of the formulation of Example 2 was added 8 g of anhydride AC-DP-1 (which is commercially available from Anhydrides and Chemicals Incorporated, N.Y., U.S.A. and which is believed to be methyl tetrahydro phthalic anhydride) and the mixture was well stirred and then placed in a PTFE mould and cured for 15 minutes at 175° C. The cooled cured epoxy was then mechanically finely ground (100 mesh).
  • AC-DP-1 which is commercially available from Anhydrides and Chemicals Incorporated, N.Y., U.S.A. and which is believed to be methyl tetrahydro phthalic anhydride
  • Example A To 10 g of the formulation of Example A was added 8 g of anhydride AC-DP-1 and the same procedure followed as in Example 4.
  • Example 4 was followed except that no additive was used with ERL 4221 E.G.
  • Example 3 To 10 g of the formulation of Example 3 was added 2.5 g poly(oxypropylene) diamine (Commercially available under the Trade Mark Jeffamine D-230 from Texaco Chemical Company, Bellaire, Tex., U.S.A.) and the composition was stirred well and then placed in a PTFE mould and cured for 15 minutes at 120° C. The cooled cured epoxy was then mechanically finely ground (100 mesh).
  • poly(oxypropylene) diamine Commercially available under the Trade Mark Jeffamine D-230 from Texaco Chemical Company, Bellaire, Tex., U.S.A.
  • Example 5 To 10 g of the formulation of Example B was added 2.5 g of poly(oxypropylene) diamine and the same procedure was followed as for Example 5.
  • the calixarene derivative of Example 1 gives similar performance to 18-crown-6 in reducing extractable sodium and potassium from cured epoxy resin when used as a 1% level additive.
  • Example 5 To 100 g Epikote 828 (Batch G) was added 1 g of 18-crown-6 and the formulation was stirred as in Example 6. To 10 g of the formulation was added 2.5 g of poly(oxypropylene)diamine and the same procedure was followed as for Example 5.
  • calixarene derivative is significantly better than 18-crown-6 at reducing extractable Na + , K + and Cl - .
  • Example G was repeated using a different batch of Epikote 828 (Batch J).
  • Example 7 To 100 g of Epikote 828 epoxy resin (Batch J) was added 1 g of the oxacalixarene derivative of Example 7. The composition was stirred well in a polyethylene beaker with PTFE-coated stirrer for 17 hours and then the same procedure as in Example 5 was followed.
  • Example 8 was followed except 5 g of the oxacalixarene derivative from Example 7 was added instead of 1 g.
  • the oxacalixarene derivative is effective at reducing extractable sodium and chloride from cured epoxy resin when used at the above indicated levels.
  • Example G was repeated using a further batch of Epikote 828 (Batch K).
  • Example 10 To 100 g Epikote 828 epoxy resin (Batch K) was added 1 g of the compound of Example 10. The composition was then stirred well in a polyethylene beaker with PTFE coated stirrer for 17 hours at room temperature, then the same procedure as in Example 5 was followed.
  • Example 11 was followed except that 5 g of amide-functional oxacalixarene of Example 10 was used in place of 1 g.
  • amide functional oxacalixarene is effective at reducing extractable sodium (and potassium and chloride) from cured epoxy resin when used at the above indicated levels.
  • a non-electronic epoxy Epikote 828 had its extractable metal ions reduced down to values expected from a good electronic epoxy resin.
  • Example 13 was followed except that 5 g of the amide-functional calixarene was used in place of 1 g.
  • the ionic impurities in the products of Examples K, 13 and 14 were measured following the MIL-A-87172 procedure described above.
  • the amide-functional calixarene is effective at reducing extractable sodium (and potassium and chloride) from cured epoxy resin when used at the above indicated levels.
  • the result from use of 1% additive is encouraging, a non-electronic epoxy Epikote 828 having its extractable metal ions reduced down to those of a good electronic epoxy.
  • Example G was repeated using a further batch of Epikote 828 (Batch L).
  • Example 15 was followed except that 5 g of 1,1-dimethylsila-17-crown-6 was added instead of 1 g.
  • the ionic impurities in the products of Example L, 15 and 16 were measured following the MIL-A-87172 procedure described above.
  • the silacrown is effective at reducing extractable sodium, potassium and chloride from cured epoxy resin when used at the above indicated level.
  • Example G was repeated with a different batch of Epikote 828 epoxy resin (Batch M).
  • Example 18 The same procedure as in Example 18 was followed except that 5% TDA-1 was employed instead of 1%.
  • This compound and other calixarene polyalkylene glycol derivatives can also be prepared by reaction of phenolic calixarene with epoxide (U.S. Pat. No. 4098717 Jul. 4 1978 by R. Buriks et al, Petrolite Corp.).
  • Example 20 A 1% level of calixarene from Example 20 was added to Epikote 828 (Batch N) resin with stirring as in Example 19 but for 17 hours to ensure complete dissolution and the composition was then treated as in Example 5.
  • Example 23 was followed except that a 5% level of calixarene derivative from Example 22 was used in place of 1%.
  • Example M The ionic impurities in Example M, 18, 19, 21 and 22 were measured following the MIL-A-87172 procedure as described above.
  • polyethylene derivatives are effective at reducing extractable sodium (and potassium and chloride) from cured epoxy resin when used at the above indicated levels.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
US07/270,136 1986-09-29 1988-11-14 Encapsulating compositions Expired - Fee Related US4908399A (en)

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IE862567A IE862567L (en) 1986-09-29 1986-09-29 Encapsulating compositions
IE2567/86 1986-09-29

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US07/088,945 Continuation-In-Part US4866198A (en) 1986-08-29 1987-08-24 Calixarene derivatives and use as accelerators in adhesive compositions
US10049487A Continuation 1985-03-28 1987-09-24

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US (2) US4908399A (de)
EP (1) EP0262910A3 (de)
JP (1) JPH01501006A (de)
KR (1) KR960004685B1 (de)
CA (1) CA1314354C (de)
IE (1) IE862567L (de)
WO (1) WO1988002386A1 (de)

Cited By (4)

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Publication number Priority date Publication date Assignee Title
US5043415A (en) * 1987-09-24 1991-08-27 Loctite (Ireland) Ltd. Nitrogen-containing oxacalixarene and calixarene derivatives, polymers including groups related to such derivatives, and use of such compounds
US5132345A (en) * 1990-12-10 1992-07-21 Harris Stephen J Ion-selective electrodes
US5210216A (en) * 1985-03-28 1993-05-11 Loctite (Ireland) Limited Calixarene and oxacalixarene derivatives and use thereof of sequestration metals
CN107043364A (zh) * 2016-02-05 2017-08-15 徐州医学院 氧杂杯[4]芳烃衍生物及其应用

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IE893986A1 (en) * 1989-12-13 1991-06-19 Loctite Ireland Ltd Polymerisable calixarene and oxacalixarene derivatives,¹polymers thereof, and use of such derivatives and polymers¹for sequestration of metals
US5434208A (en) * 1992-07-10 1995-07-18 Akzo Nobel N.V. Optically non-linear active waveguiding material comprising a dopant having multiple donor-n-acceptor systems
AU1545395A (en) * 1994-01-24 1995-08-08 Stephen J. Harris Calixarene-based compounds having antibacterial, antifungal, anticancer-hiv activity
US5840814A (en) * 1996-08-07 1998-11-24 The University Of Akron Multi-arm star polymers having a well-defined core and methods for the synthesis thereof
US6500891B1 (en) 2000-05-19 2002-12-31 Loctite Corporation Low viscosity thermally conductive compositions containing spherical thermally conductive particles
JP5979582B2 (ja) 2012-03-22 2016-08-24 セイコーエプソン株式会社 インクジェット捺染用インク組成物
CN106714464B (zh) * 2017-02-24 2019-04-02 广东成德电子科技股份有限公司 一种应用杯芳烃加工印制电路板的方法

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5210216A (en) * 1985-03-28 1993-05-11 Loctite (Ireland) Limited Calixarene and oxacalixarene derivatives and use thereof of sequestration metals
US5043415A (en) * 1987-09-24 1991-08-27 Loctite (Ireland) Ltd. Nitrogen-containing oxacalixarene and calixarene derivatives, polymers including groups related to such derivatives, and use of such compounds
US5132345A (en) * 1990-12-10 1992-07-21 Harris Stephen J Ion-selective electrodes
CN107043364A (zh) * 2016-02-05 2017-08-15 徐州医学院 氧杂杯[4]芳烃衍生物及其应用
CN107043364B (zh) * 2016-02-05 2020-04-03 徐州医学院 氧杂杯[4]芳烃衍生物及其应用

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US4957960A (en) 1990-09-18
EP0262910A3 (de) 1989-08-30
KR880701969A (ko) 1988-11-07
CA1314354C (en) 1993-03-09
IE862567L (en) 1988-03-29
EP0262910A2 (de) 1988-04-06
WO1988002386A1 (en) 1988-04-07
KR960004685B1 (ko) 1996-04-11
JPH01501006A (ja) 1989-04-06

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